Preparative electroreduction of trans-2-allyl-6-methyl(phenyl)-1,2,3,6-tetrahydropyridine.

Autor: Korotayeva, L., Rubinskaya, T., Klimkina, E., Gultyai, V., Bubnov, Yu.
Zdroj: Russian Chemical Bulletin; Apr1999, Vol. 48 Issue 4, p754-757, 4p
Abstrakt: Electrocatalytic hydrogenation of trans-2-allyl-6-phenyl-1,2,3,6-tetrahydropyridine and trans-2-allyl-6-methyl-1,2,3,6-tetrahydropyridine in 40% aqueous DMF in the presence of AcOH on a nickel cathode gave trans-6-phenyl-2-propylpiperidine and trans-2-methyl-6-propylpiperidine ((±)-epidihydropinidine), respectively. Direct electroreduction of trans-2-allyl-6-phenyl-1,2,3,6-tetrahydropyridine in anhydrous DMF on a mercury cathode afforded a 7 ∶ 5 mixture of trans- and cis-2-allyl-6-phenylpiperidine. The structure of the latter compound was confirmed by 2D NOESY spectroscopy. The possible mechanism of formation of the cis-isomer is discussed. [ABSTRACT FROM AUTHOR]
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